1-Nonanol having the structure: ##STR3## 2-undecanol having the structure: ##STR4## and 1-undecanol having the structure: ##STR5## are each useful flavorants for foodstuffs. Thus, Arctander, Perfume and Flavor Chemicals (Aroma Chemicals), Volume II, published in 1969 indicates at monograph 2348 that nonanol-1 having the structure: ##STR6## has a "refreshingly citrusy-sweet taste" and that traces of this alcohol are used in flavor compositions, e.g., imitation butter, peach, pineapple, orange and other citrus types. At monograph 3031, Arctander indicates that undecanol-1 having the structure: ##STR7## at concentrations below 20 ppm has a citrusy, oily-fruity, mildly sweet taste. Arctander indicates that both compounds having the structures: ##STR8## are useful in perfume compositions.
FENAROLI'S HANDBOOK of FLAVOR INGREDIENTS, Second Edition, Volume 2, Furia and Bellanca, published by the CRC Press, Inc. indicates that 2-undecanol having the structure: ##STR9## and stereoisomers thereof having the structures: ##STR10## are useful at 20 ppm in baked goods flavors having a fatty odor with a fruity note and a fruity taste at low concentrations. Fenaroli's Handbook further indicates that the d-stereoisomer having an optical rotation of +10.29.degree. occurs in coconut oil and the l-stereoisomer having an optical rotation of -1.18.degree. is found in rue oil. Fenaroli's Handbook further states that the l-form of the optical isomer having an optical rotation of -5.40.degree. is produced from Litsea odorifera.
Fenaroli's Handbook indicates that the 2-undecanol having the structure: ##STR11## has an FEMA number of 3246 (Flavor Extracts Manufacturing Association). Arctander indicates that the compound having the structure: ##STR12## has an FEMA number of 2789 and that the compound having the structure: ##STR13## has an FEMA number of 3097.
Accordingly, a need has arisen for an efficaceous production of natural compounds having the structures: ##STR14## and, in addition, the d-stereoisomer having the structure: ##STR15##
Forney and Markovetz, Volume 37, No. 1, 1969, BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, at pages 31-38, disclose the enzymatic conversion of 2-tridecanone to undecyl acetate using Pseudomonas aeruginosa according to the reaction sequence: ##STR16##
Forney, et al in the JOURNAL Of BACTERIOLOGY, February 1967 at pages 649-655, Volume 93, No. 2, entitled "Bacterial Oxidation of 2-Tridecanone to 1-Undecanol" using Pseudomonas 4G-9. Furthermore, Forney, et al discloses the growth of Pseudomonas 4G-9 on various substrates in Table 1 at page 652 as follows:
______________________________________ "Growth of Pseudomonas 4G-9 on various substrates Incubation Substrate days Relative Growth.sup.a ______________________________________ 2-Heptanone 12 - 2-Octanone 12 - 2-Nonanone 12 ++++ 2-Decanone 12 ++++ 2-Undecanone 12 ++++ n-Octane 12 - n-Nonane 12 ++ n-Decane 12 + n-Undecane 12 ++ n-Dodecane 12 +++ n-Tridecane 12 ++++ Nonanoate.sup.b 5 ++ Decanoate 5 +++ Undecanoate 5 ++++ Dodecanoate 5 ++++ 1-Nonanol 5 - 1-Decanol 5 ++++ 1-Undecanol 5 ++++ 1-Dodecanol 5 ++++ 1,2-Dodecanediol.sup.b 21 - 1,2-Tetradecanediol 21 ++++ ______________________________________ .sup.a Symbols: -, no growth; +, slight growth; ++, moderate growth; +++, abundant growth; ++++, maximal growth. .sup.b Substrates used at 0.1% concentration (w/v).
Nothing, however, in the prior art discloses a process for producing a mixture of alkanols defined according to the structures: ##STR17## containing at least 65 mole percent of the alkanol defined according to the structure: ##STR18## in a high yield. Nothing in the prior art shows the use of such an organism as Pseudomonas cepacia ATCC 55792 in effecting such production of a mixture of alkanols defined according to the structures: ##STR19## (wherein R.sub.1 represents methyl or n-propyl)